ASYMMETRIC-SYNTHESIS OF CHIRAL SULFINATE ESTERS AND SULFOXIDES - SYNTHESIS OF SULFORAPHANE

被引：64

作者：

WHITESELL, JK

WONG, MS

机构：

[1] Department of Chemistry, University of Texas, Austin

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 03期

关键词：

D O I：

10.1021/jo00082a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

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页码：597 / 601

页数：5

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